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In the office today we were talking about those Tootsie Roll pops. The answer from About.com:

Nobody seems to know how this rumor got started, least of all the folks at Tootsie Roll Industries in Chicago, Illinois, who have been politely deflecting mail-in requests for free Tootsie Roll Pops ever since the 1930s. They maintain there was never any sort of official promotion or contest associated with Tootsie Pop wrappers. Where the notion came from remains a mystery.

Actually, there's more to the mistakenly revered wrapper than just a star. The illustration shows an American Indian shooting an arrow at a star, and it's that Indian most people mention when they speak of the legend. I'm told about one-third of all Tootsie Pop wrappers sport the design. Why? For variety, apparently. Not much of a mystery there.

I'm not sure how commonly this happens, but readers have also reported to me that some independent grocers do unofficially honor the supposed free Tootsie Pop offer when kids bring the Indian wrappers into their stores for redemption. But it's neither sanctioned nor financed by Tootsie Roll Industries.

I saved up HUNDREDS of those in my school box with all intentions of cashing them in. The first thing I'd do when I got a tootsie pop is look for the Indian, then cram it in with the rest. I suppose at some point I expected to go into the store with my pockets full of tootsie roll pops and a big grin on my face as they unloaded thousands of tootsie roll pops for me. But luckily, I forgot about it before I tried to cash them it. It would have really crushed my spirit to save all those up only to bring them in and get a "sorry, kid, we don't do that" as a reward.